JP2000515867A - ５―（３―ブチリル―２，４，６―トリメチル）―２―（１―（エトキシイミノ）プロピル）―３―ヒドロキシシクロヘキセ―２―エン―１―オンの製造 - Google Patents
５―（３―ブチリル―２，４，６―トリメチル）―２―（１―（エトキシイミノ）プロピル）―３―ヒドロキシシクロヘキセ―２―エン―１―オンの製造Info
- Publication number
- JP2000515867A JP2000515867A JP10508328A JP50832898A JP2000515867A JP 2000515867 A JP2000515867 A JP 2000515867A JP 10508328 A JP10508328 A JP 10508328A JP 50832898 A JP50832898 A JP 50832898A JP 2000515867 A JP2000515867 A JP 2000515867A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- temperature
- reaction
- butyryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 claims abstract description 8
- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003701 inert diluent Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229950011008 tetrachloroethylene Drugs 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000004682 monohydrates Chemical class 0.000 description 4
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- -1 3-butyryl-2,4,6-trimethylphenyl Chemical group 0.000 description 1
- HBXUKEYLLIXGAE-UHFFFAOYSA-N C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(C)C=C1C Chemical compound C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(C)C=C1C HBXUKEYLLIXGAE-UHFFFAOYSA-N 0.000 description 1
- CCKSEFYKQOSRRF-UHFFFAOYSA-N CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(C(=O)CC)=C(O)C2)=C1C Chemical compound CCCC(=O)C1=C(C)C=C(C)C(C2CC(=O)C(C(=O)CC)=C(O)C2)=C1C CCKSEFYKQOSRRF-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 125000000033 alkoxyamino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU01322 | 1996-07-30 | ||
| AUPO1322A AUPO132296A0 (en) | 1996-07-30 | 1996-07-30 | Chemical process |
| PCT/AU1997/000471 WO1998004510A1 (en) | 1996-07-30 | 1997-07-25 | Preparation of 5-(3-butyryl-2,4,6-trimethyl)-2-(1-(ethoxyimino) propyl)-3-hydroxycyclohex-2-en-1-one |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000515867A true JP2000515867A (ja) | 2000-11-28 |
Family
ID=3795637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10508328A Pending JP2000515867A (ja) | 1996-07-30 | 1997-07-25 | ５―（３―ブチリル―２，４，６―トリメチル）―２―（１―（エトキシイミノ）プロピル）―３―ヒドロキシシクロヘキセ―２―エン―１―オンの製造 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6147260A (zh) |
| EP (1) | EP0915820A4 (zh) |
| JP (1) | JP2000515867A (zh) |
| CN (1) | CN1228759A (zh) |
| AR (1) | AR008122A1 (zh) |
| AU (1) | AUPO132296A0 (zh) |
| BR (1) | BR9710783A (zh) |
| TW (1) | TW416942B (zh) |
| WO (1) | WO1998004510A1 (zh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1332923C (zh) * | 2005-11-16 | 2007-08-22 | 陕西师范大学 | 2－（9－蒽基）－2－氧代乙酸乙酯的固相合成方法 |
| EP2350560B1 (en) | 2008-10-24 | 2016-02-17 | Battelle Memorial Institute | Electronic detonator system |
| WO2012177072A2 (en) * | 2011-06-24 | 2012-12-27 | Woongjin Coway Co., Ltd | Dehumidification-type air cleaner and control method thereof |
| CN112341360A (zh) * | 2020-11-19 | 2021-02-09 | 南京艾斯特医药科技有限公司 | 一种丁苯草酮衍生物及其合成方法 |
| CN112352782A (zh) * | 2020-11-19 | 2021-02-12 | 南京艾斯特医药科技有限公司 | 一种复配除草剂及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH20618A (en) * | 1982-01-29 | 1987-03-06 | Ici Australia Ltd | Herbicidal 5-(substituted phenyl)-cyclohexan-1,3-dione derivatives |
| AU3422584A (en) * | 1983-11-04 | 1985-05-09 | Ici Australia Limited | Preparation of 2-acyl-5-acyl substituted aryl-3- hydroxycyclohex--2-en-1-ones |
| NZ240662A (en) * | 1990-11-27 | 1993-04-28 | Ici Australia Operations | Preparation of the anhydrous crystalline form of fenoxydim |
| GB9111975D0 (en) * | 1991-06-04 | 1991-07-24 | Ici Plc | Chemical process |
-
1996
- 1996-07-30 AU AUPO1322A patent/AUPO132296A0/en not_active Abandoned
-
1997
- 1997-07-25 JP JP10508328A patent/JP2000515867A/ja active Pending
- 1997-07-25 US US09/230,678 patent/US6147260A/en not_active Expired - Fee Related
- 1997-07-25 BR BR9710783A patent/BR9710783A/pt unknown
- 1997-07-25 CN CN97197593A patent/CN1228759A/zh active Pending
- 1997-07-25 EP EP97931582A patent/EP0915820A4/en not_active Withdrawn
- 1997-07-25 WO PCT/AU1997/000471 patent/WO1998004510A1/en not_active Application Discontinuation
- 1997-07-30 AR ARP970103454A patent/AR008122A1/es unknown
- 1997-08-25 TW TW086110828A patent/TW416942B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TW416942B (en) | 2001-01-01 |
| EP0915820A1 (en) | 1999-05-19 |
| AR008122A1 (es) | 1999-12-09 |
| AUPO132296A0 (en) | 1996-08-22 |
| EP0915820A4 (en) | 2000-04-05 |
| US6147260A (en) | 2000-11-14 |
| WO1998004510A1 (en) | 1998-02-05 |
| BR9710783A (pt) | 1999-08-17 |
| CN1228759A (zh) | 1999-09-15 |
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